Doug Ryan

For a lot of people, sailing looks like a hobby reserved for lottery winners and folks named “Chadwick” who sip champagne on gleaming yachts. Google “sailboat” and you’ll see glossy photos of 60-foot catamarans, linen pants, and boats with names like Liquid Assets. No wonder the average person thinks, I could never afford that. But … Read more

Welcome to the Golden Era of Sailboats From the 1970s through the mid-1980s, North America saw a boom in sailboat production like never before—or since. Fueled by advances in fiberglass construction and a growing appetite for adventure on the water, manufacturers churned out thousands of sailboats annually. The result? A fleet of durable, affordable, and … Read more

What Really Counts as a Pocket Cruiser? Let’s set the record straight: when we talk about pocket cruisers, we’re not talking about 36-foot floating condos. We’re talking about small sailboats—under 30 feet long—that are seaworthy, smartly designed, and truly livable. These little giants pack more punch per foot than you might imagine and are perfect … Read more

Have you looked out over your local marina lately and noticed something missing? The hustle of rigging, the excitement of race days, the crowded start lines… all replaced by quiet docks and empty race calendars. If you feel like sailboat racing is disappearing, you’re not imagining it. Let’s take a closer look at what’s really … Read more

The Harsh Truth About Cheap Old Sailboats If you’ve been scrolling through YachtWorld or Craigslist and stumbled across a sailboat that looks “too good to be true,” there’s a good chance it is. In this post, we’re diving into the world of bad sailboats—the kinds of boats you probably shouldn’t buy, no matter how romantic … Read more

Have you ever fantasized about trading your driveway for a dock, your morning commute for a sunrise at sea, or ditching the mortgage in exchange for a tiller? For many, living on a sailboat is the stuff of dreams. For others, it’s a very real (and surprisingly doable) lifestyle. This post dives into the pros … Read more

Sailboats—romantic, serene, timeless. So why do they make up less than 1% of all boats in the U.S., and even fewer of new boat sales? Despite their charm, the sailboat lifestyle hasn’t exactly taken America by storm. In fact, their popularity has been sailing downhill since the 1980s. So what’s the deal? Let’s unpack five … Read more